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189839

Sigma-Aldrich

2,3-Dihydroxybenzaldehyde

97%

Synonym(s):

1,2-Dihydroxy-3-formylbenzene, 3-Formyl-1,2-benzenediol, 3-Hydroxysalicylaldehyde, 5,6-Dihydroxybenzaldehyde

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About This Item

Linear Formula:
(HO)2C6H3CHO
CAS Number:
24677-78-9
Molecular Weight:
138.12
Beilstein/REAXYS Number:
2041781
EC Number:
246-398-1
MDL number:
MFCD00003324
UNSPSC Code:
12352100
PubChem Substance ID:
24851400
NACRES:
NA.22

assay

97%

mp

104-108 °C (lit.)

solubility

95% ethanol: soluble 50 mg/mL, clear, colorless to greenish-yellow

SMILES string

[H]C(=O)c1cccc(O)c1O

InChI

1S/C7H6O3/c8-4-5-2-1-3-6(9)7(5)10/h1-4,9-10H

InChI key

IXWOUPGDGMCKGT-UHFFFAOYSA-N

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General description

Electrochemical oxidation of 2,3-dihydroxybenzaldehyde in methanol at various pH has been studied using cyclic voltammetry and controlled-potential coulometry.

Application

2,3-Dihydroxybenzaldehyde was used in the synthesis of copper(II) complexes of Schiff bases. It was also used in the synthesis of 2-ethoxy-3-hydroxy-4-nitrobenzoic acid.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M E Ramos-Nino et al.
Journal of applied microbiology, 84(2), 207-212 (1998-06-20)
Quantitative structure activity relationships (QSARs) were obtained describing the activity of a series of benzaldehydes against three different foodborne bacteria, Listeria monocytogenes F6861, serotype 4b, Salmonella enteritidis, Phage type 4, P167807 and Lactobacillus plantarum INT.L11. MIC values at pH 6.2
S Kato et al.
Chemical & pharmaceutical bulletin, 44(8), 1484-1492 (1996-08-01)
To confirm the proposed structures of the minor metabolites of a potential gastroprokinetic agent, mosapride, 4-amino-5-chloro-2-ethoxy-3-hydroxy-N-(2-morpholinylmethyl)benzamide (3) and the N-(5-oxo-2-morpholinyl)-methyl analogue 4 were prepared. As the common intermediate, 2-ethoxy-3-hydroxy-4-nitrobenzoic acid (15) was prepared via the regioselective ethylation of 2,3-dihydroxybenzaldehyde (10)
Investigation of the Electromethoxylation Reaction Part 2: Electrochemical Study of 3-Methylcatechol and 2, 3-Dihydroxybenzaldehyde in Methanol.
Nematollahi D and Golabi SM.
Electroanalysis, 13(12), 1008-1015 (2001)
Haitao Li et al.
The Journal of biological chemistry, 280(17), 16594-16600 (2005-02-08)
Organic nitrates have been used clinically in the treatment of ischemic heart disease for more than a century. Recently, xanthine oxidase (XO) has been reported to catalyze organic nitrate reduction under anaerobic conditions, but questions remain regarding the initial precursor
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